At Cortland, we operate with a forward-thinking approach that challenges conventional norms and actively seeks insights beyond traditional industry boundaries. As a recognized leader in the multifamily sector, our focus on performance, innovation, and disciplined execution continues to drive strong growth and market leadership. We are committed to building a best-in-class organization by empowering top talent with the resources, autonomy, and support needed to deliver results and advance their careers in a high-performance environment.

Role Overview

As the Technology Strategy & Transformation Associate, you'll help translate business problems into technology strategies, investment cases, and actionable roadmaps through analysis, research, and structured discovery. You'll work across the business and technology organization to evaluate opportunities, inform investment decisions, and measure whether delivered solutions achieve their intended outcomes.

Discovery & Business Analysis

Support discovery with business stakeholders by interviewing users, mapping current-state processes, analyzing pain points, and documenting requirements and success measures.
Translate business requests into clear problem statements and requirements that business and technical teams can evaluate and act on.
Use structured problem-solving and data to distinguish stated requests from underlying business needs and challenge assumptions when evidence supports a different approach.
Develop an understanding of business processes, economics, and systems across Cortland to identify opportunities for technology to improve business outcomes.
Coordinate across business and technology teams by preparing materials, documenting decisions, and driving action items to completion.

Roadmap & Strategic Planning

Maintain technology roadmaps and capability plans, including initiative inventories, timelines, dependencies, priorities, and status.
Analyze roadmap progress and prepare executive-ready materials that clearly communicate priorities, trade-offs, risks, and decisions needed.
Track KPIs, OKRs, adoption measures, and post-launch results to identify where performance differs from plan and support corrective action.
Develop broad exposure to AI, data, enterprise technology, and digital solutions while helping determine how technology investments support business priorities.

Business Cases & Investment Analysis

Build financial models that evaluate ROI, three-year total cost of ownership, expected benefits, and measurable baselines for technology investments.
Analyze operational and financial data to quantify business problems, establish baselines, test assumptions, and estimate potential value.
Support business cases that allow technology opportunities to be evaluated consistently and compared against competing investments.
Translate financial and operational analysis into concise recommendations and executive-ready presentations.

Technology & Market Analysis

Conduct market research to support build-vs-buy-vs-partner decisions, including market scans, vendor comparisons, SaaS assessments, feature and pricing analysis, and reference checks.
Support RFPs and vendor evaluations by documenting requirements, completing fit-gap analyses, evaluating responses, and synthesizing findings.
Research AI, data, and emerging technology capabilities to assess where they can address defined business problems and create measurable value.
Partner with AI & Analytics, Data Science, Software & Data Engineering, Enterprise & Community Applications, and Digital Experience teams to understand solution options, technical considerations, and dependencies.

Qualifications

1–3 years of experience in management or technology consulting, finance, corporate strategy or development, business analysis, product management, or a related discipline; Real estate or multifamily experience is a plus but not required.
Bachelor’s degree in business, finance, economics, information systems, computer science, or a related field.
Strong financial modeling skills in Microsoft Excel, including experience developing ROI, total cost of ownership, or comparable investment analyses.